GB792558A - Manufacture of organic peroxides - Google Patents

Manufacture of organic peroxides

Info

Publication number
GB792558A
GB792558A GB1935455A GB1935455A GB792558A GB 792558 A GB792558 A GB 792558A GB 1935455 A GB1935455 A GB 1935455A GB 1935455 A GB1935455 A GB 1935455A GB 792558 A GB792558 A GB 792558A
Authority
GB
United Kingdom
Prior art keywords
acid
hydroperoxide
carbinol
mixture
solvent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB1935455A
Inventor
Denis Cheselden Quin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Distillers Co Yeast Ltd
Distillers Co Ltd
Original Assignee
Distillers Co Yeast Ltd
Distillers Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Distillers Co Yeast Ltd, Distillers Co Ltd filed Critical Distillers Co Yeast Ltd
Priority to GB1935455A priority Critical patent/GB792558A/en
Publication of GB792558A publication Critical patent/GB792558A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C409/00Peroxy compounds
    • C07C409/16Peroxy compounds the —O—O— group being bound between two carbon atoms not further substituted by oxygen atoms, i.e. peroxides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00Preparation of peroxy compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00Preparation of peroxy compounds
    • C07C407/003Separation; Purification; Stabilisation; Use of additives

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Peroxides of the formula <FORM:0792558/IV (b)/1> where Ar is an aryl radical, R1, R2, R3 and R5 are aliphatic groups, and R5 is an aliphatic or an aryl radical, are made by reacting a hydroperoxide of the formula <FORM:0792558/IV (b)/2> with a carbinol of the formula <FORM:0792558/IV (b)/3> in a molar proportion of hydroperoxide to carbinol of from 1:0.8 to 1:1.6 and at a temperature below 60 DEG C. in solution in an aliphatic carboxylic acid which is a solvent for both reaction components and for water and in the presence of perchloric acid or sulphuric acid as catalyst, and rendering the catalyst in the reaction mixture ineffective before recovering the peroxide. Aliphatic carboxylic acid solvents mentioned are formic, acetic, propionic and butyric acids. The reaction may be effected between room temperature and 35 DEG C. with a hydroperoxide-carbonol mixture in a solution of up to 50 per cent by weight and free from water. The starting materials may be mixtures of pure hydroperoxides and carbinols, or crude hydroperoxides from the oxidation of aromatic hydrocarbons with molecular oxygen followed by removal of unreacted hydrocarbon, or crude carbinols from the chemical reduction or hydrogenation of hydroperoxides. In a preferred embodiment, a hydroperoxide-containing reaction mixture prepared by oxidation is divided into two parts, one part being reduced to the carbinol and returned to the mixture. Alternatively, the hydroperoxide-containing mixture may be hydrogenated until half is converted to the carbinol. After the condensation reaction, the catalyst is rendered ineffective by adding basic alkali-metal or alkaline earth metal compounds or alkali-metal or alkaline earth metal salts of the aliphatic acid used as solvent, and the acid solvent is then distilled off and the residue added to water or dilute aqueous alkali to separate solid peroxide. The acid solvent may be re-used after distillation. Alternatively, the condensation reaction mixture may be added directly to water. The crude product is pressed out to remove oil and recrystallized. The oil contains unreacted carbinol and may be recycled after optional distillation. In examples: (1) phenyl dimethyl carbinol, obtained by reducing cumene hydroperoxide with aqueous sodium sulphite, is reacted with cumene hydroperoxide in acetic acid and in the presence of perchloric acid to give dicumyl peroxide; (2) dicumyl peroxide is similarly obtained from a starting mixture made by oxidizing cumene with molecular oxygen at elevated temperature, removing cumene, dividing into 2 parts, hydrogenating one part in the presence of palladium on activated alumina and re-combining it with the other part; (3) sulphuric acid is used instead of perchloric acid.
GB1935455A 1955-07-05 1955-07-05 Manufacture of organic peroxides Expired GB792558A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1935455A GB792558A (en) 1955-07-05 1955-07-05 Manufacture of organic peroxides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1935455A GB792558A (en) 1955-07-05 1955-07-05 Manufacture of organic peroxides

Publications (1)

Publication Number Publication Date
GB792558A true GB792558A (en) 1958-03-26

Family

ID=10127954

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1935455A Expired GB792558A (en) 1955-07-05 1955-07-05 Manufacture of organic peroxides

Country Status (1)

Country Link
GB (1) GB792558A (en)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1124495B (en) * 1962-01-18 1962-03-01 Union Rheinische Braunkohlen Process for the preparation of di-tert-alkyl peroxides
DE1144277B (en) * 1959-03-03 1963-02-28 Konink Ind Mij Voorheen Noury Process for the production of organic peroxides
DE1155779B (en) * 1959-07-28 1963-10-17 Bergwerksgesellschaft Hibernia Process for the production of organic peroxides
US3254130A (en) * 1959-07-28 1966-05-31 Bergwerksgesellschaft Hibernia Method of preparing an organic peroxide
US3310588A (en) * 1958-08-22 1967-03-21 Konink Ind Mij Vorheen Noury & Process for the preparation of organic peroxides
US4198528A (en) * 1978-01-25 1980-04-15 Union Carbide Corporation Preparation of di-tertiary peroxides
US4322567A (en) * 1979-06-18 1982-03-30 Mitsui Petrochemical Industries Ltd. Process for production of aromatic alcohols
FR2499986A1 (en) * 1981-02-19 1982-08-20 Nippon Oils & Fats Co Ltd PROCESS FOR PRODUCING DICUMYL PEROXIDE
US4374280A (en) * 1980-02-12 1983-02-15 Euteco Impianti S.P.A. Process for the preparation of dicumyl peroxide
CN102827051A (en) * 2012-09-24 2012-12-19 金魏 Method for synthesizing dicumyl peroxide
CN103933922A (en) * 2014-04-21 2014-07-23 太仓塑料助剂厂有限公司 Reduction and condensation combined reaction device
CN109942471A (en) * 2019-04-01 2019-06-28 江苏道明化学有限公司 A kind of DCP condensation process flow

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3310588A (en) * 1958-08-22 1967-03-21 Konink Ind Mij Vorheen Noury & Process for the preparation of organic peroxides
DE1144277B (en) * 1959-03-03 1963-02-28 Konink Ind Mij Voorheen Noury Process for the production of organic peroxides
US3337639A (en) * 1959-03-03 1967-08-22 Konink Ind Mij Vorheen Noury & Process for the preparation of organic peroxides
DE1155779B (en) * 1959-07-28 1963-10-17 Bergwerksgesellschaft Hibernia Process for the production of organic peroxides
US3254130A (en) * 1959-07-28 1966-05-31 Bergwerksgesellschaft Hibernia Method of preparing an organic peroxide
DE1124495B (en) * 1962-01-18 1962-03-01 Union Rheinische Braunkohlen Process for the preparation of di-tert-alkyl peroxides
US4198528A (en) * 1978-01-25 1980-04-15 Union Carbide Corporation Preparation of di-tertiary peroxides
US4322567A (en) * 1979-06-18 1982-03-30 Mitsui Petrochemical Industries Ltd. Process for production of aromatic alcohols
US4374280A (en) * 1980-02-12 1983-02-15 Euteco Impianti S.P.A. Process for the preparation of dicumyl peroxide
FR2499986A1 (en) * 1981-02-19 1982-08-20 Nippon Oils & Fats Co Ltd PROCESS FOR PRODUCING DICUMYL PEROXIDE
US4413148A (en) * 1981-02-19 1983-11-01 Nippon Oil And Fats Co., Ltd. Process for producing dicumylperoxide
CN102827051A (en) * 2012-09-24 2012-12-19 金魏 Method for synthesizing dicumyl peroxide
CN103933922A (en) * 2014-04-21 2014-07-23 太仓塑料助剂厂有限公司 Reduction and condensation combined reaction device
CN103933922B (en) * 2014-04-21 2016-02-24 太仓塑料助剂厂有限公司 A kind of reduction condensation association response device
CN109942471A (en) * 2019-04-01 2019-06-28 江苏道明化学有限公司 A kind of DCP condensation process flow

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